GB449477A - Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series - Google Patents

Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series

Info

Publication number
GB449477A
GB449477A GB3696834A GB3696834A GB449477A GB 449477 A GB449477 A GB 449477A GB 3696834 A GB3696834 A GB 3696834A GB 3696834 A GB3696834 A GB 3696834A GB 449477 A GB449477 A GB 449477A
Authority
GB
United Kingdom
Prior art keywords
carboxylic acid
amino
anthraquinone
triazines
radicle
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3696834A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB3696834A priority Critical patent/GB449477A/en
Publication of GB449477A publication Critical patent/GB449477A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B6/00—Anthracene dyes not provided for above

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Anthraquinone vat dyes are prepared by condensing aminoanthraquinones or their derivatives with monophenyldichlor-1.3.5-triazines which are substituted in the phenyl nucleus by halogen atoms or alkoxy groups. Suitable triazines may be prepared according to Specifications 436,657 and 439,380 and include 2-chlorphenyl-, 2-p-bromophenyl-, 2-methoxyphenyl, 2-ethoxyphenyl- and 2-(2<1>.5<1>-dichlorphenyl)-4.6-dichloro-1.3.5-triazines; particularly valuable dyes are derived from those triazines containing a p-halogen- or p-methoxyphenyl group attached to the nucleus. In examples: (1) 2-p-methoxyphenyl - 4 . 6 - dichloro - 1 . 3 . 5 - triazine is condensed with 1- or 2-aminoanthraquinones, 1 - amino - 4 - methoxyanthraquinone, 1 - amino - 4 - benzoylaminoanthraquinone, 1 - amino-5-benzoylaminoanthraquinone, 1-amino-5 - p - chlorbenzoylaminoanthraquinone, 1 - amino - 5 - m - methoxybenzoylaminoanthraquinone, 1 - amino - 5 - naphthoylaminoanthraquinone or those aminoaroylaminoanthraquinones wherein the aroyl radicle is the radicle of a quinoline carboxylic acid, diphenylcarboxylic acid, anthraquinone carboxylic acid, anthraquinone benzacridone carboxylic acid, anthraquinone naphthacridone carboxylic acid, anthrapyridone carboxylic acid, anthrapyrimidone carboxylic acid, anthraquinonethioxanthone carboxylic acid or thiazolanthrone carboxylic acid; the corresponding o- or m-methoxyphenyl- and o-, m- or p-ethoxyphenyl-4 . 6 - dichloro - 1 . 3 . 5 - triazines may be used instead; (2) 2-p-chlorphenyl-4.6-dichloro-1.3.5-triazine is condensed with 1- or 2-aminoanthraquinones, 1-amino-4-benzoylamino- and/or 1-amino - 5 - benzoylaminoanthraquinones, 1 - amino - 4 - p - chlorbenzoylaminoanthraquinone, 1 - amino - 4 - o - tolylaminoanthraquinone, 1 - amino - 4 - p - ethoxybenzoylaminoanthraquinone, 1 - amino - 4 - naphthoylaminoanthraquinone or aminoaroylaminoanthraquinones wherein the aroyl radicle is that of a quinoline carboxylic acid, diphenylcarboxylic acid, anthraquinone carboxylic acid, anthraquinone benzacridone carboxylic acid, anthraquinone naphthacridone carboxylic acid, anthrapyridone carboxylic acid, anthrapyrimidone carboxylic acid, anthraquinonethioxanthone carboxylic acid or thiazolanthrone carboxylic acid; other starting materials specified as suitable are 1-amino-4-methoxyanthraquinone, 1 - amino - 3 - acylaminoanthraquinones, 1 - amino - 8 - acylaminoanthraquinones, 1 - amino - 5 . 8 - diacylaminoanthraquinones and aminoaroylaminoanthraquinones wherein the aroyl radicle is that of a pyridinoanthraquinone carboxylic acid, pyrazolanthrone carboxylic acid, selenazolanthrone carboxylic acid, or benzanthrone carboxylic acid. The products dye yellow to violet shades. British Specifications 307,947, [Class 2 (iii)], 350,575, and 372,123, German Specification 551,884, and U.S.A. Specification 1,897,428 also are referred to.
GB3696834A 1934-12-24 1934-12-24 Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series Expired GB449477A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3696834A GB449477A (en) 1934-12-24 1934-12-24 Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3696834A GB449477A (en) 1934-12-24 1934-12-24 Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series

Publications (1)

Publication Number Publication Date
GB449477A true GB449477A (en) 1936-06-24

Family

ID=10392642

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3696834A Expired GB449477A (en) 1934-12-24 1934-12-24 Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series

Country Status (1)

Country Link
GB (1) GB449477A (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2463471A (en) * 1949-03-01 Halogen-substituted guanamines
US2671785A (en) * 1952-06-27 1954-03-09 Brown triazine vat dyes
US2671786A (en) * 1952-06-27 1954-03-09 American Cyanamid Co Triazine anthrimide carbazole vat dyes
US2691018A (en) * 1951-07-10 1954-10-05 American Cyanamid Co Process of chlorinating hydroxy triazines with thionyl chloride
US2716645A (en) * 1951-05-23 1955-08-30 American Cyanamid Co Soluble esters of yellow triazine vat dyes
US2719154A (en) * 1951-05-23 1955-09-27 American Cyanamid Co Triazine vat dyes
US2729638A (en) * 1953-12-17 1956-01-03 American Cyanamid Co Vat dyestuffs of the phthaloylcarbazolo triazine series
US2735849A (en) * 1954-05-13 1956-02-21 Anthraquevone triazine vat dyestuffs
US2891971A (en) * 1951-08-01 1959-06-23 Bayer Ag Anthraquinone pigment dyestuffs
DE1062368B (en) * 1953-05-07 1959-07-30 American Cyanamid Co Process for the preparation of anthraquinonylaminotriazine kuepen dyes
US2951842A (en) * 1956-09-27 1960-09-06 Basf Ag Unitary diazine and triazine dyestuffs having two different anthraquinone substituents on the azine ring
US3022304A (en) * 1958-05-30 1962-02-20 Ciba Ltd Anthraquinone vat dyestuff containing a reactive triazing nucleus

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2463471A (en) * 1949-03-01 Halogen-substituted guanamines
US2716645A (en) * 1951-05-23 1955-08-30 American Cyanamid Co Soluble esters of yellow triazine vat dyes
US2719154A (en) * 1951-05-23 1955-09-27 American Cyanamid Co Triazine vat dyes
US2691018A (en) * 1951-07-10 1954-10-05 American Cyanamid Co Process of chlorinating hydroxy triazines with thionyl chloride
US2891971A (en) * 1951-08-01 1959-06-23 Bayer Ag Anthraquinone pigment dyestuffs
US2671785A (en) * 1952-06-27 1954-03-09 Brown triazine vat dyes
US2671786A (en) * 1952-06-27 1954-03-09 American Cyanamid Co Triazine anthrimide carbazole vat dyes
DE1062368B (en) * 1953-05-07 1959-07-30 American Cyanamid Co Process for the preparation of anthraquinonylaminotriazine kuepen dyes
US2729638A (en) * 1953-12-17 1956-01-03 American Cyanamid Co Vat dyestuffs of the phthaloylcarbazolo triazine series
US2735849A (en) * 1954-05-13 1956-02-21 Anthraquevone triazine vat dyestuffs
US2951842A (en) * 1956-09-27 1960-09-06 Basf Ag Unitary diazine and triazine dyestuffs having two different anthraquinone substituents on the azine ring
US3022304A (en) * 1958-05-30 1962-02-20 Ciba Ltd Anthraquinone vat dyestuff containing a reactive triazing nucleus

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